Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H12O6 |
| Molecular Weight | 324.2843 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C2C(=O)C3=C(OC2=C4[C@@H]5C=CO[C@@H]5OC4=C1)C=CC=C3O
InChI
InChIKey=UTSVPXMQSFGQTM-DCXZOGHSSA-N
InChI=1S/C18H12O6/c1-21-11-7-12-13(8-5-6-22-18(8)24-12)17-15(11)16(20)14-9(19)3-2-4-10(14)23-17/h2-8,18-19H,1H3/t8-,18+/m0/s1
Sterigmatocystin is a mutagenic and carcinogenic mycotoxin initially produced by species of Aspergillus. Sterigmatocystin is a precursor of aflatoxin B1. In vitro, Sterigmatocystin activates ATM, p53, and Chk2 and damages DNA, inducing G2 phase cell cycle arrest; this mechanism may also involve PI3K/Akt/mTOR signaling. In vivo, chronic administration of sterigmatocystin decreases levels of glutathione, ascorbic acid, and α-tocopherol and increases levels of ROS, increasing lipid peroxidation.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Histone modifications and chromatin dynamics: a focus on filamentous fungi. | 2008-05 |
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| Analysis of Aspergillus nidulans metabolism at the genome-scale. | 2008-04-11 |
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| LC-MS/MS multi-method for mycotoxins after single extraction, with validation data for peanut, pistachio, wheat, maize, cornflakes, raisins and figs. | 2008-04 |
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| Botryolides A-E, decarestrictine analogues from a fungicolous Botryotrichum sp. (NRRL 38180). | 2008-03 |
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| Functional analyses of heterotrimeric G protein G alpha and G beta subunits in Gibberella zeae. | 2008-02 |
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| Evidence for horizontal transfer of a secondary metabolite gene cluster between fungi. | 2008-01-24 |
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| Reciprocal oxylipin-mediated cross-talk in the Aspergillus-seed pathosystem. | 2008-01 |
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| Mycotoxins in rice. | 2007-10-20 |
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| A novel regulator couples sporogenesis and trehalose biogenesis in Aspergillus nidulans. | 2007-10-03 |
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| Origin and distribution of epipolythiodioxopiperazine (ETP) gene clusters in filamentous ascomycetes. | 2007-09-26 |
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| Regulations relating to mycotoxins in food: perspectives in a global and European context. | 2007-09 |
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| Dioctatin A is a strong inhibitor of aflatoxin production by Aspergillus parasiticus. | 2007-08 |
|
| Guanine alkylation by the potent carcinogen aflatoxin B1: quantum chemical calculations. | 2007-08 |
|
| Kipukasins, nucleoside derivatives from Aspergillus versicolor. | 2007-08 |
|
| Analytical method for the determination of sterigmatocystin in grains using high-performance liquid chromatography-tandem mass spectrometry with electrospray positive ionization. | 2007-07-20 |
|
| Gene duplication, modularity and adaptation in the evolution of the aflatoxin gene cluster. | 2007-07-09 |
|
| 1H and 13C NMR assignments for two anthraquinones and two xanthones from the mangrove fungus (ZSUH-36). | 2007-05 |
|
| [Experimental study on the carcinogenic effects of sterigmatocystin in new born BALB/c mice]. | 2007-04 |
|
| Computer aided boar semen motility analysis for cereulide detection in different food matrices. | 2007-02-28 |
|
| The effect of Egyptian honeybee propolis on the growth of Aspergillus versicolor and sterigmatocystin biosynthesis in Ras cheese. | 2007-02 |
|
| Aspergillus nidulans VeA subcellular localization is dependent on the importin alpha carrier and on light. | 2007-01 |
|
| Tumour-specific expression of CYP2W1: its potential as a drug target in cancer therapy. | 2007-01 |
|
| Secondary metabolite profiling, growth profiles and other tools for species recognition and important Aspergillus mycotoxins. | 2007 |
|
| Biodiversity of Aspergillus species in some important agricultural products. | 2007 |
|
| Polyphasic taxonomy of Aspergillus section Usti. | 2007 |
|
| The current status of species recognition and identification in Aspergillus. | 2007 |
|
| Recombination hotspots flank the Cryptococcus mating-type locus: implications for the evolution of a fungal sex chromosome. | 2006-11-03 |
|
| Analysis of the dermatophyte Trichophyton rubrum expressed sequence tags. | 2006-10-11 |
|
| Secondary metabolic gene cluster silencing in Aspergillus nidulans. | 2006-09 |
|
| Biosynthesis of dothistromin. | 2006-09 |
|
| Biochemical analysis of oxidative stress in the production of aflatoxin and its precursor intermediates. | 2006-09 |
|
| Aflatoxigenicity in Aspergillus: molecular genetics, phylogenetic relationships and evolutionary implications. | 2006-09 |
|
| Association algorithm to mine the rules that govern enzyme definition and to classify protein sequences. | 2006-06-15 |
|
| A polyketide synthase gene required for biosynthesis of the aflatoxin-like toxin, dothistromin. | 2006-05 |
|
| A novel biosensor for sterigmatocystin constructed by multi-walled carbon nanotubes (MWNT) modified with aflatoxin-detoxifizyme (ADTZ). | 2006-05 |
|
| Heterotrimeric G protein signaling and RGSs in Aspergillus nidulans. | 2006-04 |
|
| Aspergillus ustus infections among transplant recipients. | 2006-03 |
|
| FluG-dependent asexual development in Aspergillus nidulans occurs via derepression. | 2006-03 |
|
| The phosducin-like protein PhnA is required for Gbetagamma-mediated signaling for vegetative growth, developmental control, and toxin biosynthesis in Aspergillus nidulans. | 2006-02 |
|
| Oxylipins act as determinants of natural product biosynthesis and seed colonization in Aspergillus nidulans. | 2006-02 |
|
| Characterization of aflatoxin-producing fungi outside of Aspergillus section Flavi. | 2006-01-07 |
|
| Fungi recovered from Slovakian poultry feed mixtures and their toxinogenity. | 2006 |
|
| Kinetics of the oxidoreductase involved in the conversion of O-methylsterigmatocystin to aflatoxin B1. | 2006 |
|
| Development of a liquid chromatography/tandem mass spectrometry method for the simultaneous determination of 16 mycotoxins on cellulose filters and in fungal cultures. | 2006 |
|
| Comparison of gene expression signatures of diamide, H2O2 and menadione exposed Aspergillus nidulans cultures--linking genome-wide transcriptional changes to cellular physiology. | 2005-12-20 |
|
| Fundamental contribution of beta-oxidation to polyketide mycotoxin production in planta. | 2005-08 |
|
| [Effects of sterigmatocystin on HLA- I expression of human peripheral blood mononuclear cells in vitro]. | 2005-07 |
|
| [Histogenesis of lung adenocarcinoma induced by oral adminstration of mycotoxins in mice]. | 2005-05 |
|
| Aspergillus mycotoxins and their effect on the host. | 2005-05 |
|
| Hexanoate synthase, a specialized type I fatty acid synthase in aflatoxin B1 biosynthesis. | 2001-10 |
Patents
Sample Use Guides
Rats: The incidence of chromosome aberrations in bone-marrow cells increased and reached the maximum level at 12 h after an intraperitoneal injection of 10(-1) mM(31.2 mg)/kg body weight of Sterigmatocystin and decreased gradually to the original level after 96 h.
Route of Administration:
Intraperitoneal
The human hepatoma cell line HepG2 a significant dose-dependent increase of DNA strand breaks was found after treatment with Sterigmatocystin (3 and 6 uM) respectively for 1 h. Increases in ROS level and the expression of 8-OHdG were also observed. A statistically significant increase in AO fluorescence intensity was observed in cells treated with Sterigmatocystin (1.5, 3 and 6 uM) for 1 h.
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18227
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STERIGMATOCYSTIN
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D013241
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SUBSTANCE RECORD
